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Water → 2-(2-tert-Butyl-1H-tetrazol-5-yl)phenyltri-n-butylstannane

HRID 1440463
Notes
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Reaction equation

HRID 1440463 reaction equation
C([N:5]1[C:9]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2Br)=[N:8][N:7]=[N:6]1)(C)(C)C.[Li]C[CH2:19][CH2:20][CH3:21].[CH2:22]([Sn:26](Cl)([CH2:31][CH2:32][CH2:33][CH3:34])[CH2:27][CH2:28][CH2:29][CH3:30])[CH2:23][CH2:24][CH3:25].O.[CH2:37]1COCC1>>[C:20]([N:7]1[NH:6][N:5]=[C:9]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[Sn:26]([CH2:31][CH2:32][CH2:33][CH3:34])([CH2:27][CH2:28][CH2:29][CH3:30])[CH2:22][CH2:23][CH2:24][CH3:25])[NH:8]1)([CH3:19])([CH3:21])[CH3:37]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 5

HCID 962WaterHCID 8028TetrahydrofuranHCID 15096Tributyltin Chloride2×HCID 218408841-tert-Butyl-5-(2-bromophenyl)-1H-tetrazoleHCID 178418339Butyllithium

Product 1

HCID 676965402-(2-tert-Butyl-1H-tetrazol-5-yl)phenyltri-n-butylstannane
Yield 45%

Procedure

To a cooled (-78° C.) solution of 1-tert-butyl-5-(2-bromophenyl)-1H-tetrazole (12.3 g, 0.043 mol), prepared as described in Step 3 of the Example 3 alternative synthesis, in THF (80 mL) was added 1.6M nBuLi in hexanes (32.7 mL, 0.052 mol). After 1 h, tri-n-butyltin chloride (17.1 g, 0.052 mol) was added and stirring was continued for 3 h at -78° C. The mixture was warmed to room temperature and stirred for 18 h. Water was added and the mixture was extracted with ether. The combined extracts were washed with water, brine, dried (MgSO4), and concentrated to give a brown oil. Excess tri-n-butyltin chloride and remaining starting material were removed by distillation under high vacuum to give 9.6 g (45%) of product as a brown oil.

Workup

  1. customprepared
  2. waitwas continued for 3 h at -78° C
  3. stirringstirred for 18 h
  4. extractionthe mixture was extracted with ether
  5. washThe combined extracts were washed with water, brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated
  8. customto give a brown oil
  9. customwere removed by distillation under high vacuum

Sources & evidence

ORD record
ord-8c08ab3b4c0f447e9732c003643ec903
Source dataset
uspto-grants-1996_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05498776

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes